Mercury derivatives of nitro-paracresols



Patented Jan. 1,,1935

30121 7 "1 e (on-2 George .waw zll lii ladelphia, Pat, assigliiorfljhbbottLa-hormgzuflorth Chicago, 111 corv, I

. mater" 27.5 grams of 2-nitro-para-cresolprepared by. diazotization ofz-nitro-para-toluldine' and demo l we 1 CRESO S wwfl e Y.

beptmiiwtanp u which hav'been found to"beespecially lefieotive banterbacteriostatic agents, 'nartieumbati hilfectiou's diseases, and relatesx A 54,293;.graritdLScDEmber 2 "and reissued as" 0. 1,1,563 dated, Jan:grandam nd: atn i 3 1 10 "51 ante May ;24; 192.7 ,theref-aredescribedloer ereu'ry 'derivatives'of 'nitro-ortho-fcresol. Thesederivatives were" found to have excellent properties as,'bactericides';lfiowever; oonti'n ued researeh has dvelopedthe fact tnjercury derivatives of enitr paramresol andthe r various isomers" maylikewise'be prepared and that c'er tain of these last-mentionedderivatives possess markedly :superiorrqualities to thosebfthe prev'i- 1t 'ously known derivatives 2 jl 'hese newnitro oresol f derivativesjdiffer from eacliloth' ,someti miesfto a considerabl; ektentiintheirph'ys'ical, chemica'rana bacteriGIoEiAl'propE erties, and may berepresented by tlie typical .a formula: R fH for the mono-merouryderivatives, and

R-(HgXDi tions mai bag-norm H Fii (ooc-cng C H CH -NO -OH-IkCOO-CHH-CHCOOH f The'hydroxy-mercuri derivatives are prefer- V ably formed asalkali metal salts, in alkaline solution, as follows: 60

The halogen derivatives may be formed by treating either the acetoxy,hydroxy or anhydrohydroxy derivatives with a halide acid, thus:

60 tion:

mercury derivatives oi initron mi'nedswby; removing-a small pontion olare,

.rnixture- "is cooled and" filtered."

'whiehasfiltered'and cooled! mama 615mm;

curi derivative accordingQto' the following reac-' A composition withsulphuric acid (Berichte-15, I 2980) are dissolved in 7 .2 gmti-NaOH and1200 co. m of H20. To this is added'5'7 gm. of mercuric ace-' tate,dissolvedin 210 ccsoffwater and 12 cc; of

acetic'acidr a The mixture'isvqboiled nut-u I a lo cresol :isWXHDIEIEIYECjIOHMtBdpfihiS debencipitate and solution from the reactionmixture;

and adding to this a, solution of sodium hy-.- droxide. If a clearyellow to orange red solution isobtained f the fnerouration fis'eompaae; v *The cipitate isthen assame a; ution';

mercurifi-i'tro Qoresolseparate: 11 is: repeated twioe'and the-finalbatch of cfystiis V withaetbne-and driedfi 'Iheproduct; 5jmerouri-2enitro-para-cresolj eonlstlrig o greenish-yellow needlesg ldarkening; at 21 2 0.,

below QOO" C., may be repreand not melting sented:

20-55 ts .51 4 1.1.v po e nde infl t !':-&nd;4 smnw0 sodium im-skies a eI r not. o; ob a nv a Fclear so ut o the wol'this jsolutionyadd adualwedi'luteacetio:

It is an amorphous powder of orange color, in! soluble in water, solublein dilute alkalies. Color of alkaline solution (1 500) is orange yellow.CH2'CH3-"NOQ OHHECI+NGCI+ H O;

Example 2 I toluidme (Berichte-Zi, 1960) or by nitration of para-cresolinq benzene medium (Beri'chte- -4i), 4324) aridcemploying tlie methodandquantities ortho-cresol. However, on longer exposure, the formercompound shows-a much: higher bactericidalflvalue'thari rnetaphen.vThus, the inhibitive effect of this compound against staphylococcus1*..aureus is twice as strong as that of metaphen 5 t u18 and12v m-Changes" and variations coming within the spirit of my invention willdoubtless suggest themdescribed in Example 1, I obtain S-acetoxy-mercuri-3-nitro-para-creso1:

"SBIVBSJitOHthOSE skilled in the art. Hence, I do H c o H id notf wishto -be limited to the specific embodi- 10 ments -disclosed herein oruses mentioned except I to the ezgtent set; forth in the appendedclaims, lemon-yellow aggregates of prisms, darkeningat hmghh'are to be.1nterprieted as broadly as the 260 0 not melting below 300 c andanhydroStat? ihe art W111 i I claim as my invention: 15 im Q" ?*F@- V 1. Amercury compound of a nitro-para-cresol, Ha' characterized byahighbactericidal and bacterio at cwz mex v Q2; anhydro-hydroxy-mercuricompound of afnitrQ paraf-dresol, characterized by a high bac-f g0tericidal andbacteriostatic value. 3. An hydroxy-mercuri compound of a1nitro para-cresol, characterized by a high bactericidalandbacteriojstatic'value;' I

A mercury compound 01' Z-nitro-para-cresol, characterized by amghbactericidal and bacteriostaticvalue'i V. mercury compound of3-nitro-para.-creso1, characterized by a highbactericidal andbacteriopara-cres ordinarily do. not form;,di-

0 in. ,h p V H .U static'value; v i 3.0

mer ryp 9 mis b t;wh n2+mtr r 1 rel 6 "A: batericidal substance havingthe fore 9 .1 m rc atedtw thalm lec l so cu c muiaf *3 I J e tataandftll t r l n m rcumcq u r r I crysta lized: .reevti e i om laqalzaceti lqi s Q e e ewcr si l e subsfi e-i 9 ie w where Xis an alkali metal. 3ana sis P FQ eS ba e -i -i a px mel'- $1 7. 'Anhy'dro'hydrox'y-mercuri-2-nitro.-paral rq-pa awq esolndznmx h l e rw n edcres'olfwhich maybe represented by the struc f lowin ul icturarrorihifla: w

N v V i 11 N03 CH:C O Q-Hg Hg-O o 0-c Hg 3 i e v i 5 .H

The compounds'desc'ribed above are usually my mih f u t 6 f,; dispensedin mm of their Sodium Salts in c'resoljwhich may be represented bythestrucaqueous solution, the preparation of which will fi a gfmmbecbvio'ustoithose' skilledin'the ma 1r. i '-As*'an{ezi'ample -of'j thebactericidal properties of -the' subfst'ance's' described above;rerrence ay be made to laboratory tests" of the anhdro-hydreary-mercuric niprcwycresbi product from one hour-"s eiipo'suret'o'bac ri a-is substa ri aw tially equal' to metaphn'; theproductdescr'ibed 5? in myPate nt No 1,554,293, reissuedas 5105 11563;thelatter in eiciiryderivat ej'dr mm: GEORGEW. RAIZISS; c

(iii 3 I} Certificate of Correction ed that error appears in the printedspecification of the above Hiring correction as follows: Page 2, firstco umn,1'n the graphic en lines 40 and 45, a lathe extreme right offormula, for OH nd th e said Letters t g read e read Wlth h1s corre tlontherein e m to the record of the case 1n the Patent Ofiic lgned andsealedthis 22nd f Januar A. 1935.

[sEAL] LESLIE FRAZER,

v 7 January 1 1935 GEORGE W. RAIZ ISS It is hereby certifi

